


A Gentleman Never Tells

by the_only_education_worth_having



Series: Requested Fics [27]
Category: Actor - Fandom, American Actor, Greys Anatomy Cast, RPF - Fandom
Genre: F/M, First Dates, Kissing, New love, Set Ups, blind dates
Language: English
Status: Completed
Published: 2018-09-25
Updated: 2018-09-25
Packaged: 2019-07-17 10:55:07
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,464
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16094228
Author URL: https://archiveofourown.org/users/the_only_education_worth_having/pseuds/the_only_education_worth_having
Summary: Jesse goes on his first first date in years





	A Gentleman Never Tells

**Author's Note:**

> Jesse Williams imagine where Sarah Drew plays matchmaker for you two?❤️❤️  
> greysanatomyimaginesworld

Sarah knocked on the trailer door quickly before entering the trailer. Jesse was sat on his couch playing video games but he looked up when she entered and smiled at her before pausing the game and putting the controller down and saying ‘hey.’  
‘Hey you,’ she said with a smile as she dropped down onto the couch beside him and nudged him on the shoulder, ‘so… how did it go?’  
‘Good,’ he said looking at her before he broke out in a smile, ‘really good.’  
‘So come on then. What happened?’  
‘Well…’

Jesse sat at the bar with a beer in hand. He hadn’t been on a first date in ages and so he was more nervous than ever. He had spent at least half an hour choosing what shoes to wear with his outfit tonight and he’d gotten to the restaurant at least twenty minutes earlier than he needed to.

He’d been single for a while now but he hadn’t been ready to date despite one of his closest friends, Sarah’s, constant attempt to set him up on blind dates. He had always refused until about a week ago. It was only last week that he found himself being able to picture him with someone, more than just thinking someone was good looking, he saw himself having a relationship. Of course when he had mentioned this around his friend her eyes had lit up and she had gotten ecstatic almost immediately and told him she had the perfect girl for him. He rolled his eyes, he didn’t believe her but her utter enthusiasm about the prospect made it impossible for him to say no. He couldn’t believe he had managed to hold out on her for that long. So with little to no work, Sarah set up the date and here he was.

He was about to order another drink, he’d gone through his last like lightning trying to implement some dutch courage when he felt the lightest tap on his shoulder. He turned to find a woman behind him before he could say anything she spoke, ‘Jesse?’  
‘That’s me,’ he said, ‘Y/N?’  
She nodded and smiled at him as he explained that he had gotten them a table and the two of them headed towards the maître d. As they walked he took her in. She was incredibly cute. She had wide eyes and ample lips. Her breasts were quite large but they were in well proportion to her figure which he couldn’t help but admire in the dress she was wearing. It clung to her figure, accentuating every curve and causing that flutter inside him he hadn’t felt in months.

The maître d seated them and read them the specials and they ordered drinks before he disappeared.  
‘So,’ Y/N started, ‘Sarah tells me you don’t do this very often?’  
‘Yeah,’ Jesse said nervously, ‘I’ve been off the dating scene for quite a while. How about you?’  
‘Hit and miss mostly. I’ve been dating around for about six months but nothing has ever come to fruition.’  
‘How come?’  
‘Never really clicked with anyone. And the modern world you can’t just meet anyone off the street it’s got to be dating app and websites and things. And there are some weirdo’s out there.’  
‘Really?’ Jesse chuckled, ‘hoping you don’t think I’m one of them.’  
‘Only time will tell,’ she said cocking a sultry eyebrow.’

‘So you liked her?’ Sarah asked excitedly.  
‘I liked her.’  
‘What happened then?’  
‘Well, we got into dinner and talked about our careers and stuff.’

‘So you work with Sarah?’  
‘Yeah, for about 8 years now. She’s a real gem.’  
‘Yeah, I’ve seen the show. The two of you work really well together.  
‘You’ve seen Greys,’ he asked, ‘should I ask what you think or will I be disappointed?’  
‘You won’t be. After Sarah got her part I binged watched all the seasons for her. I mean I won’t say it isn’t far fetched sometimes but my God it’s addictive and the acting’s brilliant.’  
‘Thanks,’ he chuckled, ‘it’s far-fetched but that’s the hook. How do you know Sarah?’  
‘We went to college together. We’ve been friends longer than I care to remember,’ she giggled, ‘ it makes me feel old.’  
‘You old? You look about twenty-two,’ Jesse ribbed, ‘how old are you?’  
‘Thirty-six, you?’  
‘Thirty-seven, what do you do, by the way, I never asked.’  
‘I’m a lawyer, please spare me the jokes, I’ve heard them all,’ she said as she sipped on her drink and looked at the menu.  
‘What sort of lawyer?’  
‘I work with mostly state-appointed cases, so it’s not like hot shot cases and rich people murdering their spouses and what not. It’s usually low-level criminals and people who don’t have much choice.’  
‘So you try and help?’  
‘Best I can,’ she shrugged, ‘it’s like screaming at a brick wall most of the time.’  
‘I can imagine.’

‘What else did you talk about?’  
‘A lot of things, we talked about my divorce, my kids. Her kids. She told me about growing up back east and things like that.’  
‘The what happened?’  
‘We left the restaurant and I walked her to her car.’  
‘And?’  
‘And….’

The rain pelted down outside the restaurant doors and Jesse and Y/N merely stood and watched it, powerless to do much else. ‘You know what’s ironic? I left my umbrella in my car because the weather report on the way here said there was no chance of rain,’ she said causing Jesse to laugh. He had enjoyed himself over the course of the night. He and Y/N had really clicked and they had a lot of things in common. She even took it well when he spoke to her about his romantic history, which Sarah had neglected to inform her of, she handled the shock well and even asked to see pictures of his kids. She was incredibly witty and had this amazing laugh that he loved to listen to. Listening to her storytelling he could tell she was sweet and kind. He liked her. He really liked her and he thought that he could be the gentlemen and walk her to her car, and then ask for her number. If he were lucky he may even be able to kiss her goodnight but now the rain had halted that idea. The urgency to get into her car surely would take any of the romance out of it.  
‘Where did you park?’ she asked, looking at him with a smile.  
‘In that corner over there,’ he said pointing to the SUV in the corner of the lot.  
‘Really? That’s right next to mine, spooky,’ she said, ‘ah screw it. Let’s just run for it. It’s only water right?’ before he could reply he felt a hand grasp his and pull him forward. He couldn’t help but smile as she lead him outside into the freezing cold rain and ran at full speed towards the corner of the lot. He was impressed as he ran behind her, his hand still in hers, as she jogged along without falling in her high heels.

They reached their cars in no time and stood in the gap between them. Though the rain hadn’t cleared at all Jesse was beyond caring. He was happy, stood there in the freezing cold feeling the water leach into his skin and making him shiver. Y/N stood in front of him and smiled, though she was wearing a thin dress the heat that radiated off the man in front of her was enough to keep her warm. She braved the waters, feeling that Jesse probably wasn’t as brave as he used to be due to his problems on the dating scene, and leant forward to place a hand on his arm as she said, ‘It’s been a good night. I’ve really enjoyed myself.’  
‘Me too.’  
‘We should do it again sometime,’ she let the idea dangle between them hoping he would snap it up. It was a moment before anyone spoke, ‘we should, I can give you my number?’  
‘I’d like that,’ she said, inching closer as Jesse’s hands reached out and touched her hips. They were soaked by this point and it was hard to hear each other over the noise of the rain hitting the cars next to them, ‘but you know what I would like even more?’  
‘What?’ he asked, with his famed coy smile as his baby blue eyes glinted with wonder. She leaned up to his ear and whispered, ‘I’d like you to kiss me.’

‘So!’ Sarah practically shouted causing Jesse to lean back to stop himself being deafened, ‘what did you do?!’  
‘A gentleman never tells,’ Jesse chuckled, ‘but after that, let’s just say we’re going out again Tuesday night.’


End file.
